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Base Pairing of 8‐Aza‐7‐deazapurine‐2,6‐diamine Linked via the N(8)‐Position to the DNA Backbone: Universal Base‐Pairing Properties and Formation of Highly Stable Duplexes when Alternating with dT
Author(s) -
He Junlin,
Seela Frank
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1340::aid-hlca1340>3.0.co;2-h
Subject(s) - chemistry , phosphoramidite , pairing , base pair , duplex (building) , oligonucleotide , stereochemistry , diamine , dna , base (topology) , nucleobase , pyrimidine , polymer chemistry , biochemistry , mathematical analysis , physics , superconductivity , mathematics , quantum mechanics
The unusually N 8 ‐glycosylated pyrazolo[3,4‐ d ]pyrimidine‐4,6‐diamine 2′‐deoxyribonucleoside ( 3 ) was synthesized and converted to the phosphoramidite 11 . Oligonucleotides were prepared by solid‐phase synthesis, and the base pairing of compound 3 was studied. In non‐self‐complementary duplexes containing compound 3 located opposite to the four canonical DNA constituents, strong base pairs are formed that show ambiguous pairing properties. The self‐complementary duplex d( 3 ‐T) 6 ( 34 ⋅ 34 ) is significantly more stable than d(A‐T) 6 .